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Details

Stereochemistry RACEMIC
Molecular Formula C4H6O5
Molecular Weight 134.0874
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Malic acid

SMILES

OC(CC(O)=O)C(O)=O

InChI

InChIKey=BJEPYKJPYRNKOW-UHFFFAOYSA-N
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula C4H6O5
Molecular Weight 134.0874
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Malic acid is a tart-tasting organic dicarboxylic acid that contributes to the taste of many sour or tart foods such as apples. Sodium Malate is the sodium salt of Malic Acid. Malic Acid and Sodium Malate can be found in a wide range of cosmetics and personal care products. Sodium Malate functions as a skin conditioning agent-humectant. As a food additive, Sodium Malate has the E number E350. Sodium Malate has demonstrated protective effect on cisplatin-induced toxicity in mice. Sodium malate could become a useful agent for the reduction of CDDP-induced toxicity, particularly nephrotoxicity and hepatotoxicity.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Curative
ACERBINE

Approved Use

Acerbine solution is suitable for the treatment of superficial skin injuries, such as burns, scalds, sunburn, wounds and abrasions.
Doses

Doses

DosePopulationAdverse events​
1 % 8 times / day multiple, topical
Studied dose
Dose: 1 %, 8 times / day
Route: topical
Route: multiple
Dose: 1 %, 8 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
600 mg 2 times / day multiple, oral
Studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Variation of isoenzyme and RAPD patterns in Candida albicans morphological mutants with altered colony ultrastructure.
2001
Isocitrate dehydrogenase, malate dehydrogenase, and glutamate dehydrogenase from Archaeoglobus fulgidus.
2001
Survey of normal appearing mouse strain which lacks malic enzyme and Nad+-linked glycerol phosphate dehydrogenase: normal pancreatic beta cell function, but abnormal metabolite pattern in skeletal muscle.
2001 Apr
Physiological basis of reduced AL tolerance in ditelosomic lines of Chinese Spring wheat.
2001 Apr
Phlebotomine sandflies in Venezuela. V. Review of the genus Brumptomyia (Diptera: Psychodidae), with description of the female of Brumptomyia devenanzii, re-description of the male and isozymatic profile.
2001 Apr
Effect of an antidiabetic extract of Catharanthus roseus on enzymic activities in streptozotocin induced diabetic rats.
2001 Aug
Structural analyses of a malate dehydrogenase with a variable active site.
2001 Aug 17
Abscisic acid induces a decline in nitrogen fixation that involves leghaemoglobin, but is independent of sucrose synthase activity.
2001 Feb
High level expression of C4-specific NADP-malic enzyme in leaves and impairment of photoautotrophic growth in a C3 plant, rice.
2001 Feb
Exercise and ovarian steroid hormones: their effects on mitochondrial respiration.
2001 Feb 16
Substrate and cofactor binding to fluorescently labeled cytoplasmic malate dehydrogenase.
2001 Feb 9
Computerized analysis of cytochemical reactions for dehydrogenases and oxygraphic studies as methods to evaluate the function of the mitochondrial sheath in rat spermatozoa.
2001 Jan
[Lactate and malate dehydrogenase activity in the sterlet and Russian sturgeon under conditions of the widespread muscular pathology].
2001 Jan-Feb
Malo-ethanolic fermentation in grape must by recombinant strains of Saccharomyces cerevisiae.
2001 Jul
Thyroid hormone--sympathetic interaction and adaptive thermogenesis are thyroid hormone receptor isoform--specific.
2001 Jul
Massive sequence comparisons as a help in annotating genomic sequences.
2001 Jul
pH-dependent investigations of vanadium(V)-peroxo-malate complexes from aqueous solutions. In search of biologically relevant vanadium(V)-peroxo species.
2001 Jul 16
Transcriptome meets metabolome: hierarchical and metabolic regulation of the glycolytic pathway.
2001 Jul 6
The first examples of (S)-2-hydroxyacid dehydrogenases catalyzing the transfer of the pro-4S hydrogen of NADH are found in the archaea.
2001 Jul 9
The effect of nucleotides and mitochondrial chaperonin 10 on the structure and chaperone activity of mitochondrial chaperonin 60.
2001 Jun
An NMR-based metabonomic approach to the investigation of coelomic fluid biochemistry in earthworms under toxic stress.
2001 Jun 29
Non-photosynthetic 'malic enzyme' from maize: a constituvely expressed enzyme that responds to plant defence inducers.
2001 Mar
Methyl pyruvate initiates membrane depolarization and insulin release by metabolic factors other than ATP.
2001 Mar 1
Myxothiazol induces H(2)O(2) production from mitochondrial respiratory chain.
2001 Mar 2
[Properties of gluconeogenesis enzymes from flatworms].
2001 Mar-Apr
Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.
2001 May
Cloning and functional characterization of the 5' flanking region of the human mitochondrial malic enzyme gene. Regulatory role of Sp1 and AP-2.
2001 May
Possible involvement of protein phosphorylation in aluminum-responsive malate efflux from wheat root apex.
2001 May
Patents

Sample Use Guides

Apply Acerbine solution (malic acid, salicylic acid, benzoic acid) to the wound or damaged skin two or more times daily or moisten the dressing again. Once scar formation begins, one application a day is generally sufficient.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:50:51 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:51 GMT 2025
Record UNII
817L1N4CKP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Malic acid
EP   FCC   II   INCI   MI   NF   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
E-296
Preferred Name English
MALIC ACID [USP IMPURITY]
Common Name English
MALIC ACID, DL-
Common Name English
POMALOUS ACID
Common Name English
INS NO.296
Code English
MALIC ACID [VANDF]
Common Name English
MALATE
Common Name English
MALIC ACID [USP-RS]
Common Name English
DL-MALIC ACID
Common Name English
HYDROXYBUTANEDIOIC ACID, (±)-
Systematic Name English
MALIC ACID [FCC]
Common Name English
NSC-25941
Code English
INS NO. 296
Code English
E296
Code English
(±)-MALIC ACID
Common Name English
MALIC ACID [II]
Common Name English
MALIC ACID [EP MONOGRAPH]
Common Name English
HYDROXYBUTANEDIOIC ACID [HSDB]
Common Name English
INS-296
Code English
MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
Common Name English
D,L-MALIC ACID
Common Name English
Malic acid [WHO-DD]
Common Name English
HYDROXYSUCCINIC ACID
Common Name English
MALIC ACID [MI]
Common Name English
2-HYDROXYBUTANEDIOIC ACID
Systematic Name English
MALIC ACID [NF]
Common Name English
Classification Tree Code System Code
CODEX ALIMENTARIUS (GSFA) INS-296
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
DSLD 2323 (Number of products:281)
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
JECFA EVALUATION INS-296
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
LOINC 13770-3
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
LOINC 25113-2
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
JECFA EVALUATION DL-MALIC ACID
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
CFR 21 CFR 184.1069
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
EPA PESTICIDE CODE 51101
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
LOINC 75068-7
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
Code System Code Type Description
NSC
25941
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
RXCUI
70612
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
ALTERNATIVE
SMS_ID
100000091777
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
HSDB
1202
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
DRUG BANK
DB12751
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
MESH
C030298
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
CAS
617-48-1
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
SUPERSEDED
RXCUI
29209
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
NCI_THESAURUS
C80654
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
CONCEPT Industrial Aid
WIKIPEDIA
MALIC ACID
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
CHEBI
30797
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
210-514-9
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID0027640
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
RS_ITEM_NUM
1374601
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
CHEBI
15595
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
FDA UNII
817L1N4CKP
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
PUBCHEM
525
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
DAILYMED
817L1N4CKP
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
CHEBI
6650
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
EVMPD
SUB14455MIG
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
MERCK INDEX
m7041
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1455497
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
CAS
6915-15-7
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
EVMPD
SUB59600
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
230-022-8
Created by admin on Mon Mar 31 17:50:51 GMT 2025 , Edited by admin on Mon Mar 31 17:50:51 GMT 2025
ALTERNATIVE
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY